Dimethylformamide dimethyl acetal → HCID 69731813, compound

HRID 1064838Notes

Reaction equation

HRID 1064838 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[C:9]([C:12]1[C:20]2[O:19][C:18]([S:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][N:27]([CH2:30][C:31]([NH:33][C:34]4[C:39]([CH:40]([CH3:42])[CH3:41])=[CH:38][CH:37]=[CH:36][C:35]=4[CH:43]([CH3:45])[CH3:44])=[O:32])[CH2:26][CH2:25]3)=[N:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)(=[O:11])[CH3:10]>CN(C=O)C>[CH3:3][N:4]([CH3:6])[CH:5]=[CH:10][C:9]([C:12]1[C:20]2[O:19][C:18]([S:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][N:27]([CH2:30][C:31]([NH:33][C:34]4[C:35]([CH:43]([CH3:45])[CH3:44])=[CH:36][CH:37]=[CH:38][C:39]=4[CH:40]([CH3:41])[CH3:42])=[O:32])[CH2:28][CH2:29]3)=[N:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 22272831HCID 22272831, compound

Product 1

HCID 69731813HCID 69731813, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Dimethylformamide dimethylacetal (146 mg, 1.2 mmol) was dropped into a solution of 2-[4-[2-(7-acetylbenzoxazol-2-ylthio)ethyl]piperazin-1-yl]-N-(2,6-diisopropylphenyl)acetamide (214 mg, 0.4 mmol) in DMF (15 ml), followed by stirring at 80° C. for 4 hours. The reaction solution was allowed to cool and extracted with ethyl acetate. The organic layer was washed with water and diluted hydrochloric acid solution successively and dried over sodium sulfate to provide 245 mg of crude 2-[4-[2-[7-(3-dimethylaminoacryloyl)benzoxazol-2-ylthio]ethyl]piperazin-1-yl]-N-(2,6-diisopropylphenyl)acetamide.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and diluted hydrochloric acid solution successively
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-64169bdcd649446b9163bb2247e411b5
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

Loading…